Refine Search
Sort by
$1,785,000
4 Beds 4 Baths O6431500 MLS
Perfectly positioned on the 8th fairway of the renowned Golden Bear Golf Course in Keene's Pointe, this stunning Victorian estate offers timeless elegance, exceptional craftsmanship, and breathtaking golf course views. A grand foyer welcomes you with an impressive circular staircase, setting the stage for the home's sophisticated design and gracious living spaces. The gourmet kitchen is a chef's dream, featuring a large center island, breakfast bar, premium finishes, and seamless flow into the main living areas, where a cozy wood-burning fireplace creates a warm and inviting atmosphere. A wraparound covered front porch adds classic Southern charm and provides the perfect place to relax and unwind. Designed for effortless indoor-outdoor living, the spectacular backyard is an entertainer's paradise. Enjoy a sparkling saltwater pool, gas-heated spa, newly installed outdoor kitchen, and a retractable screened lanai—all overlooking the picturesque fairways of the Golden Bear Golf Course. Located within the highly sought-after gated community of Keene's Pointe, residents enjoy 24-hour guarded security, an award-winning golf course, tennis courts, a resort-style community pool, and an exceptional lifestyle in one of Central Florida's premier neighborhoods. This extraordinary residence offers the perfect blend of luxury, comfort, and breathtaking surroundings.

8241 Tibet Butler Drive, Windermere

Listing courtesy of GOLFPARK PROPERTIES. 407-566-9482

$6,900,000
5 Beds 6 Baths O6430931 MLS
Stately and elegant lakefront estate showcasing the best of Isleworth West. This grand home spans more than 7,000 square feet with 5 bedrooms- of which, four are on the ground floor – plus office, gym, library, storage room, upstairs media room and downstairs bonus room, perched along Lake Louise, the only lake on the Butler Chain surrounded by Isleworth. Expansive formal and living spaces are highlighted by picturesque lake views. The seamless flow from room to room takes full advantage of a layout built for living. The chef’s kitchen with island, gas cooktop, stainless appliances, hidden walk-in pantry, and built-in hutch offer an abundance of space for entertaining or family gatherings. The primary retreat offers an escape from the ordinary with peaceful lake views, a master bath with jetted tub, garden and water view shower, and a showstopping two-story custom closet that will be the envy of all. The executive office with wood walls and built-in shelving offers a luxurious setting for attending to business from home. Three secondary bedrooms on the main floor are all spacious and feature ensuite bathrooms. Upstairs is a fourth bedroom, gym, library, and open media room with balcony. Outdoor amenities include a screened patio with summer kitchen, oversized resort-style pool with travertine decking, large green space, and private dock with covered boat lift plus dock-mounted jet-ski lifts, and 3-car garage. Home also includes a full-house generator. This coveted location within Isleworth West offers an intimate setting with a limited number of homesites and no pass-through traffic. Community is regarded as Central Florida’s most exclusive address with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional membership opportunities.

6055 Louise Cove Drive, Windermere

Listing courtesy of STOCKWORTH REALTY GROUP. 407-909-5900

$525,000
3 Beds 2 Baths A4702367 MLS
Welcome to this beautiful maintained traditional-style home in the highly desirable Town of Windermere, Florida, just minutes from the renewed Butler-Chain of Lakes. Nestled in a quiet, peaceful neighborhood, this 3-bedroom, 2-bathroom home offers 1,926 square feet of comfortable living space with thoughtful upgrades throughout. The updated kitchen features renovated cabinetry, while both bathrooms have been tastefully upgraded. The spacious primary suite includes a large walk-in closet, and elegant crown molding adds character to the primary bedroom and dining area. Additional highlights include the roof installed four years ago, beautiful tile flooring throughout the home with carpet in the living room and bedrooms, stylish glass shower doors in the secondary bathroom, and an attached two-car garage. Every detail reflects the pride of ownership and care this home has received over the years. Residents also enjoy access to fantastic community amenities, including a swimming pool, tennis courts, and a basketball court, providing opportunities for recreation just steps from home. This is a peaceful retreat with the opportunity to enjoy the sought-after Windermere style. This home is a beautiful place to call your own.

6679 Duncaster Street, Windermere

Listing courtesy of FLATFEE.COM. 954-965-3990

$675,000
5 Beds 5 Baths O6429931 MLS
Gorgeous former model home situated on an oversized corner lot with a beautiful private swimming pool! Designed for comfortable living and entertaining, this spacious home offers an exceptional layout and a highly desirable location near Walt Disney World, shopping, dining, and everyday conveniences. Fresh interior and exterior paint gives the home a clean, refreshed feel. The first floor features a generously sized primary bedroom with an en-suite bathroom. The open-concept kitchen overlooks the expansive family room, creating the perfect setting for relaxing afternoons, family gatherings, and entertaining guests. Upstairs, you will find a spacious bonus room with beautiful views, a large full bathroom, two additional bedrooms, and a conveniently located laundry room with the washer and dryer included. Step outside to enjoy the impressive pool and patio area, ideal for entertaining or embracing the Florida lifestyle. The separate detached building offers a garage on the first floor and a private bedroom with a full bathroom above. This versatile space is perfect for a guest suite, home office, studio, or additional living area. A truly special home offering abundant space, flexibility, and an outstanding location with convenient access to Central Florida’s world-famous attractions!

7236 Penkridge Lane, Windermere

Listing courtesy of ATLAS BLUE REALTY INC. 321-948-2242

$3,500,000
4 Beds 6 Baths O6430755 MLS
Welcome to the exclusive gates of Isleworth, golf front estate offers over 7,600 square feet of refined luxury living overlooking the fairway of the renowned Isleworth Golf & Country Club, one of the worlds most prestigious golf club communities, this championship course was designed by Arnold Palmer and set along the Butler Chain of Lakes. The neighborhood is defined by beautifully landscaped scenery, sweeping water views, and exceptional 24 hour guard gated privacy. This estate offers exceptional potential supporting four beds, six baths, a private office, inside gym, approached by a private driveway with ample guest parking and a 4 car garage. The two story residence opens with a regal marble foyer and fountain feature. Inside, vaulted ceilings, skylights, and wall to wall sliding glass doors fill the main living areas with natural light while framing views of the pool, sauna, golf views and rolling fairways beyond. A grand fireplace and wet bar create an inviting space for entertaining. The chef’s kitchen centers on a dramatic island and is highlighted by a striking copper range hood, warm cabinetry, and an open eat in layout designed for both everyday living and hosting. Above the garage, a private accessory dwelling unit provides flexible secondary living space or maids living. Each of the spacious bedrooms offers its own view and is finished with marble baths. A dedicated home gym adds further convenience. Exceptional amenities and sophisticated living in the world renowned community of Isleworth.

5524 Worsham Court, Windermere

Listing courtesy of ATLIS REALTY GROUP LLC. 863-212-5455

$3,400,000
6 Beds 7 Baths S5154885 MLS
Spectacular Private Gated Lakefront Estate on Lake Olivia in Windermere - From the moment you enter through the custom iron gates, you are welcomed into a private lakefront estate unlike any other. Nestled on 1.75 acres along the shores of Lake Olivia, this custom-built Mediterranean residence showcases Tuscan-inspired architecture, mature landscaping, and a winding paver drive creating a true sense of arrival and privacy. Offering six bedrooms, all with ensuite bathrooms, including a private attached mother-in-law suite, this estate features an ideal floor plan with nearly all living spaces and five bedrooms conveniently located on the main level, with the sixth bedroom and bonus/media space upstairs. Elegant craftsmanship is showcased throughout with stone accents, travertine and granite finishes, and refined details. The primary retreat features French doors opening to the screened lanai with pool and lake views, dual custom closets, and a luxurious bath complete with stone flooring, tiled shower, jetted tub with fireplace and mounted TV, dual vanities, private water closet with bidet, and illuminated makeup area. The attached sixth bedroom suite offers a private side entrance, separate kitchen, sitting area, and serene lake views, perfect for guests or multigenerational living. The gourmet chef’s dream kitchen features double islands, granite countertops, premium appliances including a full-size professional Wolf 6-burner and griddle gas range with double ovens, 48” Sub-Zero Pro refrigerator/freezer with lit glass door, food warmer drawer, additional convection oven, wine fridge, and butler’s pantry. Additional highlights include a separate media/games room upstairs, formal living and dining spaces, spacious laundry room with pantry storage, and an oversized 3-car garage with keypad entry, side entrance, and epoxy flooring. The expansive 1,200+ square-foot screened lanai spans the rear of the home and is fully protected with 8 remote hurricane shutters. Enjoy multiple gathering areas overlooking the pool and lake, a summer kitchen with Viking grill, hood, fridge and sink, stone fireplace, teak ceilings, and a breathtaking lagoon-style saltwater pool with heart-shaped spa. Recent enhancements totaling over $200,000 include all-new light fixtures and ceiling fans, whole-house generator with automatic transfer capability restoring power in under 15 seconds during an outage, Leaf Guard gutter system, new AC system, remote hurricane shutters, roof tile servicing and sealing for pest protection, newly installed side pavers, and fresh interior paint. Take in the stunning lake views from the oversized boathouse and screened dock room, featuring a motorized boat lift with direct access to Lake Olivia — a private spring-fed lake with no public access, sandy bottom, and exceptional opportunities for boating, skiing, and fishing. A rare opportunity to own a private lakefront estate with no HOA offering architectural elegance, exceptional entertaining spaces, modern upgrades, and the tranquility of one of Central Florida’s most desirable private lakes. Conveniently located near world-class shopping, major highways, and area attractions. Move-in ready and available for immediate showings with 360 Tour and floorplan available.

9679 Westover Roberts Rd, Windermere

Listing courtesy of TONYDAVIDSHOMES.COM, LLC. 321-559-1145

$400,000
3 Beds 3 Baths O6430630 MLS Na BLDG.
ABSOLUTELY STUNNING WINDERMERE END-UNIT TOWNHOME! Welcome home to this exceptional end-unit townhome, perfectly positioned in one of the most desirable locations within the community. Nestled against tranquil wooded conservation and lush green space, this home offers a rare sense of privacy with no front neighbors and direct access to a scenic community walking path. One of the largest floor plans in the neighborhood, this beautifully maintained 3-bedroom, 2.5-bath residence is filled with natural light, creating a bright, open, and inviting atmosphere throughout. The spacious open-concept kitchen, dining, and living area is ideal for both everyday living and entertaining. The kitchen is tastefully upgraded with granite countertops, a stylish tile backsplash, rich wood cabinetry, and quality flooring. Best of all, there is no carpet anywhere in the home! All kitchen and laundry appliances are included, making this home truly move-in ready. The thoughtfully designed floor plan provides each bedroom with convenient access to a bathroom. The generous primary suite features dual vanities, a large walk-in closet, and a spacious ensuite bath designed for comfort and functionality. Step outside to enjoy the private fenced courtyard leading to the oversized rear-entry two-car garage with a pedestrian door, offering both convenience and privacy. Enjoy low-maintenance living with an HOA that covers exterior maintenance, landscaping, roof maintenance, pest control, and access to the beautiful resort-style community pool and clubhouse. Located in the heart of Windermere, this home offers an unbeatable location with top-rated A schools and easy access to Disney, Lakeside Village, Horizon West, Winter Garden Village, shopping, dining, and major roadways. This is a rare opportunity to own one of the finest townhomes to come on the market in quite some time. Don't miss your chance to make this exceptional home yours!

12303 Langstaff Drive, Windermere

Listing courtesy of REAL BROKER, LLC. 855-450-0442

$6,650,000
5 Beds 7 Baths O6429164 MLS
Positioned along the back nine of Isleworth’s renowned championship golf course, this exceptional estate spans nearly 7,000 square feet and has been thoughtfully reimagined through an extensive three-year renovation. Showcasing timeless architecture with a fresh, sophisticated aesthetic, the residence blends elegant European influences with light-filled interiors, superior craftsmanship and refined contemporary finishes. Custom French doors open to a breathtaking foyer, where soaring double-height ceilings introduce beautifully redesigned living spaces. Beautiful new flooring, designer lighting and a striking stone fireplace create an elegant backdrop, while expansive windows frame views of the sparkling pool, spa and outdoor living areas. Designed for both everyday living and effortless entertaining, the home's central gathering spaces include a warm and inviting family room with a fully modernized media display featuring handmade wooden slats and a custom fireplace, seamlessly connected to the spectacular new kitchen. Anchored by an oversized island, the kitchen features custom cabinetry, premium Wolf and Sub-Zero appliances and generous seating, creating a welcoming space for family and guests alike. The primary suite serves as a tranquil retreat, offering direct access to its own lanai along with a beautifully renovated spa-inspired bath featuring a walk-in shower, soaking tub and dual vanities. Four spacious en-suite guest bedrooms provide exceptional comfort and privacy, while the home office offers an ideal work-from-home setting. Upstairs, the original 19th Hole-inspired game room showcases a custom bar and opens to a private balcony overlooking the 16th green. Outside, meticulously manicured grounds provide a private resort-style setting. Offering an impressive sense of scale, the expansive covered lanai features soaring volume ceilings and beautiful new oversized stone tile flooring that elevate the space's timeless architecture. A fully equipped summer kitchen overlooks the custom swimming pool and spa, while generous areas for lounging and dining create an inviting extension of the home's beautifully reimagined interiors. Together, they create the perfect environment for year-round outdoor entertaining and relaxation in one of Central Florida's most prestigious golf communities.

9921 Lake Louise Drive, Windermere

Listing courtesy of ISLEWORTH REALTY LLC. 407-909-9000

$379,900
3 Beds 3 Baths O6428484 MLS N/A BLDG.
SELLER OFFERING $5000 FLEXIBLE CONCESSIONS- CAN BE APPLIED TOWARD CLOSING COSTS, RATE BUYDOWNS, PREPAIDS, OR PROPERTY ENHANCEMENTS. NEW ROOF TO BE INSTALLED WITIHIN UPCOMING MONTHS BY HOA. Privacy is hard to find in townhome living—and this Windermere home delivers it. Backing to peaceful conservation with no rear neighbors, this beautifully maintained 3-bedroom, 2.5-bath townhome in sought-after Berkshire Park offers 1,644 square feet, a private fenced courtyard, and a detached two-car garage—all in the heart of Windermere. Inside, the beautifully appointed kitchen features granite countertops, 42-inch cabinetry, stainless steel appliances, and a newly purchased refrigerator and microwave. A spacious dining area and walk-in pantry provide plenty of room for everyday living and entertaining, while French doors open directly to the private courtyard. Surrounded by picturesque views of mature trees and conservation, this outdoor space offers a peaceful setting for morning coffee, dining al fresco, entertaining, or simply unwinding at the end of the day. The kitchen flows seamlessly into the spacious living room, creating a comfortable and inviting gathering space highlighted by an electric fireplace that is included with the home. Upstairs, the spacious primary suite offers a walk-in closet, dual vanities, and an oversized walk-in shower. Two additional bedrooms and a full bathroom provide flexibility for family, guests, or a dedicated home office. Berkshire Park offers a true neighborhood lifestyle with a community pool, tennis and basketball courts, scenic walking trails, tranquil ponds, and mature landscaping. HOA services include landscaping, structural exterior maintenance, and pest control, adding to the ease of low-maintenance townhome living. Ideally located near Walt Disney World, Winter Garden Village, Hamlin Town Center, shopping, dining, major roadways, and area schools, this move-in-ready home combines privacy, convenience, and the Windermere lifestyle in one exceptional location. Come experience the peaceful setting and see what makes 12914 Vennetta Way feel like home.

12914 Vennetta Way, Windermere

Listing courtesy of BHHS FLORIDA REALTY. CapriceAtwell@BHHSFloridaRealty.com

$2,300,000
5 Beds 5 Baths O6428604 MLS
Exceptional Keene's Pointe Pool Home with Rare Multi-Generational Layout with a Pond View! Welcome to this exceptional 5-bedroom, 4.5-bath residence nestled on one of the most peaceful cul-de-sacs in the Keene's Pointe community. Perfectly positioned on a stunning water-view homesite with an expansive backyard and exceptional privacy, this home offers an incredibly flexible floor plan rarely found in today's market. The thoughtfully designed layout places the main living areas, private office, and spacious primary suite all on the first floor, creating the perfect setup for everyday living. Upstairs, three generously sized bedrooms and a large bonus room are tucked away, providing an ideal retreat for family or guests. Adding even more versatility, a completely separate detached in-law suite features a spacious bedroom and full bath, making it perfect for extended family, guests, a private home office, or live-in accommodations. Major updates provide peace of mind for years to come, including a brand-new roof, new glass sliders and windows, new septic system and drain field, A/C in 2024, and 2021 water heater. Keene's Pointe is one of Central Florida's premier 24-hour guard-gated communities, set along the pristine Butler Chain of Lakes. Residents enjoy beautifully maintained parks, playgrounds, walking trails, private boat launch access to Lake Burden, fishing piers, and a vibrant community atmosphere. Optional membership to the renowned Golden Bear Club provides access to a Jack Nicklaus Signature golf course, tennis and pickleball courts, a resort-style swimming pool, fitness center, and more. Families will also appreciate the community's proximity to top-rated schools, upscale shopping, fine dining, world-famous attractions, and Orlando International Airport.

9904 Brentford Court, Windermere

Listing courtesy of LAKESIDE REALTY WINDERMERE INC. 407-876-5575

$3,100,000
4 Beds 5 Baths O6428441 MLS
Virtually Staged. Welcome to 12102 Montalcino Circle, an exceptional custom built waterfront estate located in one of Windermere's most sought after gated communities, Casa Del Lago. Perfectly positioned at the end of a quiet cul-de-sac on 1.41 acres along the shores of Lake Burden, this extraordinary residence is offered fully furnished and showcases breathtaking water views, nightly Disney fireworks from the backyard, and a private boat dock complete with water, electric, and a boat lift. Designed for year round enjoyment, the outdoor living space features a heated pool and spa, a covered summer kitchen with a built in grill, sink, refrigerator, and bar seating, along with a fire pit, creating the ultimate lakefront retreat from the moment you arrive. Inside, timeless craftsmanship and thoughtful design are showcased throughout. Just beyond the foyer, the formal dining room welcomes guests with a coffered ceiling and is complemented by a wet bar with a dedicated wine closet, creating an elegant setting for entertaining. Nearby, a private office or den offers a quiet retreat for work or relaxation. The spacious living room is highlighted by a matching coffered ceiling, a gas fireplace, and pocket sliding glass doors that disappear completely, creating a seamless transition between the indoor living areas and the outdoor entertaining spaces. The beautifully appointed kitchen blends style and function with granite countertops, stainless steel appliances, a natural gas cooktop, a tile backsplash, and a breakfast nook overlooking the pool and sparkling waters of Lake Burden. The first floor primary suite is a private sanctuary with breathtaking lake views and direct access to the lanai. The primary bath features separate vanities, a soaking tub, an oversized walk in shower with dual shower heads, and an expansive walk in closet. A second first floor bedroom with its own en suite bath, walk in closet, and peaceful pond views provides an ideal space for guests or multigenerational living. Upstairs, a generous bonus room serves as the perfect gathering space, complete with a fireplace, wet bar, and sliding glass doors that open to a private balcony overlooking Lake Burden. One upstairs bedroom features its own en suite bath, while the second is conveniently located just steps from a full bath, providing comfortable accommodations for family and guests. Perfectly positioned just minutes from downtown Windermere, Winter Garden Vineland Road, Restaurant Row, Walt Disney World, and Orlando International Airport, this remarkable estate offers an exceptional combination of privacy, luxury, and convenience.

12102 Montalcino Circle, Windermere

Listing courtesy of EXP REALTY LLC. 888-883-8509

$475,000
3 Beds 3 Baths S5154426 MLS Na BLDG.
Welcome to this charming two-story townhome in the highly desirable Windermere Trails community! Featuring 3 bedrooms, 2.5 bathrooms, and 1,631 sq. ft. of comfortable living space, this home offers an open-concept main floor seamless for daily living and entertaining. The kitchen is appointed with granite countertops, stainless steel appliances, a breakfast bar, and a spacious pantry. Upstairs, you will find all bedrooms, including a private owner's suite complete with an an-suite bathroom and generous closet space. Enjoy outdoor living with your private enclosed courtyard connecting the home to the detached 2-car garage. Community amenities include a resort-style pool, splash pad, dog park, playground, and scenic walking trails. Superb location with top-rated Orange County schools nearby and easy access to Disney, Horizon West dining, and major expressways. Schedule your private showing today!

8386 Iron Mountain Trail, Windermere

Listing courtesy of MY REALTY GROUP, LLC.. 786-847-7421

$579,000
3 Beds 2 Baths O6427997 MLS
Virtually Staged. Discover this beautifully maintained 3-bedroom, 2-bath corner-lot home in Windermere. Surrounded by tree-lined streets and a welcoming neighborhood atmosphere, this home combines timeless charm with everyday convenience. Enjoy relaxing on the covered front porch, perfect for morning coffee, visiting with the neighbors or unwinding after a long day. Inside, the thoughtfully designed floor plan offers comfortable living spaces that are ideal for both everyday life and entertaining. The home features a galley style kitchen positioned between a cozy breakfast nook and the dining room, allowing for both casual and traditional dining options. The split-bedrooms provide added privacy. The on-suite primary bathroom features a soaking tub, dual vanities and a separate stand alone shower. The shower glass and tile were replaced in the fall of 2025. The home features real bamboo hardwood flooring in all interior areas except the kitchen, nook, bathrooms and laundry room. From the living room, open the sliders and step into your oversized patio. This patio has a generous covered area and a screened portion, allowing you to comfortably enjoy outdoor living while being protected from the Florida sun, weather and insects. The fully vinyl fenced backyard has two access gates and is ideal for pets, play or outdoor gatherings. New gutters and water heater were added in 2026, offering added peace of mind. Residents of this community enjoy access to a resort-style pool, basketball court, tennis/pickleball courts and a walking path, offering endless opportunities for recreation, relaxation and an active lifestyle. Whether you are searching for your first home, looking to downsize, or simply wanting to enjoy the charm and lifestyle that Windermere is known for, this property offers an exceptional opportunity in a highly sought-after location. Conveniently located near excellent schools, shopping, dining, theme parks and major roadways, this home offers easy access to everything Central Florida has to share. Don’t miss this opportunity - schedule your showing today.

13231 Roxboro Road, Windermere

Listing courtesy of LA ROSA REALTY KISSIMMEE. 407-930-3530

$7,500,000
6 Beds 8 Baths O6426995 MLS
Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional craftsmanship, and resort-style amenities come together in one of Windermere's most coveted locations. Built in 2024 and spanning approximately 6,900 square feet under air (10,400 total square feet), this custom residence sits on a rare one-acre homesite along the iconic, paved Second Avenue, renowned for its festive holiday displays, spectacular sunsets, and unmatched charm. Designed for both everyday luxury and grand scale entertaining, this 6 bedroom, 7.5 bathroom home offers en-suite bedrooms with walk-in closets, including a private first floor guest suite. The stunning primary retreat features a spa inspired bathroom and a private balcony overlooking the lake, creating the perfect setting to enjoy breathtaking sunsets and nightly Disney fireworks. The heart of the home is a designer chef's kitchen featuring exquisite Cristallo countertops, premium Miele appliances, and seamless flow into the expansive living and entertaining spaces. A dramatic floating wood staircase with a striking stone accent wall serves as an architectural centerpiece, while an elevator provides effortless access to every level. Additional highlights include a custom onyx sink in the powder bath, elegant 8-foot solid wood core doors throughout, motorized blinds, and laundry rooms on both the first and second floors. Step outside to experience a true private resort. The heated infinity edge saltwater pool features a unique acrylic glass viewing wall, allowing swimmers to enjoy underwater lake views unlike anything else. The expansive summer kitchen is equipped with two oversized Big Green Egg grills, a hibachi grill, and generous entertaining areas perfect for hosting unforgettable gatherings. A spacious game room with a full bar, dedicated fitness room, and professionally designed dog run complete the home's exceptional lifestyle offerings. Boating enthusiasts will appreciate the impressive two story private dock with multiple lifts, providing direct access to the famed Butler Chain of Lakes. Car collectors will love the oversized four car garage with an automotive lift, an additional golf cart garage, and an exceptionally long driveway offering abundant guest parking, a rare luxury on Second Avenue. Constructed with impact-rated windows and doors, spray foam insulation, and energy-efficient systems, this home was thoughtfully built to provide superior comfort, security, and efficiency. Combining impeccable design, world-class amenities, spectacular waterfront views, and one of the finest addresses in Central Florida, this remarkable Lake Butler estate represents a rare opportunity to own a nearly new custom home in one of Windermere's most sought after neighborhoods. Be sure to click on the virtual tour links.

724 W 2nd Avenue, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396

$1,225,000
5 Beds 3 Baths O6426164 MLS
Virtually Staged. **SANDY SHORES SANCTUARY** A rare 1934 Windermere Landmark on the Butler Chain of Lakes. Rich in history and timeless charm, this one-of-a-kind canal-front home offers a rare opportunity to own a piece of Old Windermere. Privately nestled beneath a canopy of oak trees in the exclusive Sandy Shores enclave, one of Windermere's most private waterfront communities, this 5-bedroom, 3-bath residence offers direct canal access to Lake Butler. Blending historic charm with modern comfort, the home has been thoughtfully updated with a remodeled kitchen and bathrooms, 2024 HVAC systems, a 2017 roof, 2021 & 2017 water heaters, a 2020 septic drain field, and a 2026 well tank. Relax on the screened-in porch or waterfront deck while enjoying peaceful canal views, all with no HOA and just minutes from downtown Windermere, Windermere Preparatory School, championship golf, upscale dining, and Orlando's premier attractions. This is an extraordinary opportunity where history, privacy, and lakefront living converge.

12085 Sandy Shores Drive, Windermere

Listing courtesy of ALL REAL ESTATE & INVESTMENTS. 407-917-8206

$1,595,000
4 Beds 4 Baths O6425494 MLS
Welcome to this impeccably designed, all-on-one-floor luxury custom home located in one of the most sought-after gated communities of Windermere, Casa Del Lago, where timeless Mediterranean architecture meets refined Florida living. This exceptional home offers four bedrooms and four full bathrooms and is thoughtfully designed with custom details, designer features, modern décor, graceful indoor-outdoor flow, and resort-style outdoor living. From the moment you arrive, the home makes a lasting impression with its classic barrel tile roof, stone-accented exterior, brick-paved driveway, lush landscaping, and charming private courtyard entry. Inside, you are greeted with style and elegance, welcomed by soaring ceilings, elegant archways, rich crown molding, designer lighting, beautiful travertine flooring throughout the main living areas, and hardwood flooring in the bedrooms. The bright and inviting formal living and piano room features tray ceiling details and expansive sliding glass doors that open to the covered lanai and pool area, creating a seamless connection between indoor comfort and outdoor relaxation. The open layout flows beautifully into the family room, making it ideal for everyday living and entertaining. The family room showcases a beautiful onyx wall with an electric fireplace and built-in surround sound system, creating a warm and elegant focal point for the home. The gourmet kitchen offers granite countertops, custom cabinetry, premium appliances, a built-in oven, microwave, refrigerator, dishwasher, disposal, gas cooking, kitchen exhaust hood, and a water filtration system. It connects to the butler’s area, which leads to the formal dining room. The private owner’s suite is thoughtfully separated from the secondary bedrooms, offering a sense of personal sanctuary and a peaceful retreat with generous space and a luxurious bathroom featuring dual vanities, a garden tub, and a frameless glass shower. Additional bedrooms provide comfort and flexibility for family, guests, or a home office. The home also features custom built-in closet shelving, providing excellent storage and organization. The outdoor living area is truly special, featuring a screened covered lanai with rich wood ceiling detail, built-in surround sound system, gas grill, outdoor vent hood, dining area, and lounge space overlooking the sparkling heated pool and jacuzzi/spa. Surrounded by tropical landscaping, palm trees, privacy walls, fencing, water features, and multiple seating areas, the backyard creates a private resort-style setting perfect for relaxing, entertaining, and enjoying beautiful Florida evenings — with the added charm of being close enough to enjoy Disney-area fireworks. Additional upgrades include a Tesla charger connection and thoughtful custom features throughout the home. This home offers convenient access to Disney theme parks, world-class entertainment, shopping, restaurants, major highways, and some of the area’s top public and private schools, including nearby Windermere Preparatory School. A rare opportunity to own a custom luxury home with timeless design, elegant finishes, privacy, and exceptional indoor-outdoor living in one of Central Florida’s most desirable locations. This home is truly a dream come true.

12417 Montalcino Circle, Windermere

Listing courtesy of LA ROSA REALTY LLC. 321-939-3748

$629,900
5 Beds 4 Baths O6426386 MLS Milano BLDG.
Virtually Staged. Welcome home to 11773 Bella Milano Ct — a 5-bedroom, 3.5-bath residence on a quiet cul-de-sac in the sought-after gated community of Belmere Village. Enjoy rare privacy with a wooded conservation view at the rear, bordering a park with no through-access, and a lot size just under a quarter acre. Inside, engineered hardwood and tile flooring flow through the main living areas (one living room is carpeted), beneath vaulted and 9'4"+ ceilings on the first floor. The spacious primary suite is a true retreat, featuring a garden tub, separate shower, dual vanities, private toilet closet, walk-in closet, and an adjoining sitting room with its own exterior entrance to the backyard. Four additional bedrooms deliver flexible space for family, guests, or a home office. The kitchen features stainless steel appliances. Major systems are well maintained: both HVAC units have been replaced (2023 and 2026), and the tile roof was resurfaced in 2023 with no major repairs since. A 2-car garage completes the home. Belmere's $130/month HOA includes a gated entrance, community pool, clubhouse, tennis courts, basketball court, sand volleyball court, playground, and fitness center — all within Windermere's top-rated school zone and minutes from the Butler Chain of Lakes and Winter Garden's Plant Street district.

11773 Bella Milano Court, Windermere

Listing courtesy of KELLER WILLIAMS ADVANTAGE 2 REALTY. murraycoleman@kw.com

$350,000
3 Beds 3 Baths O6425885 MLS 7712 BLDG.
This Berkshire Place townhome offers a thoughtfully arranged two-story layout with three bedrooms, inviting living spaces, and a convenient Windermere location. The covered front porch opens to a bright living room with a ceiling fan, while the adjoining dining area creates an easy connection to the kitchen. Dark wood cabinetry, stainless-steel appliances, recessed lighting, a window above the sink, and a raised breakfast bar provide a functional kitchen setup with space for casual seating. A half bathroom completes the main level. Upstairs, the primary suite features windows on two sides, a walk-in closet, and an en suite bathroom with a long dual-sink vanity and enclosed shower. Two additional bedrooms, each with a ceiling fan and closet, share a full bathroom with a tub and shower combination. Just beyond the dining area, double glass doors open to an enclosed brick-paver courtyard that provides a low-maintenance setting for outdoor dining, grilling, or container gardening. The courtyard also connects directly to the rear-entry two-car garage, creating convenient access between the home and parking area. Berkshire Place offers tree-lined sidewalks, a playground, a community pool overlooking the water, and sports courts, adding opportunities to enjoy the outdoors close to home. Located in Windermere’s Lakeside Village area, the townhome is convenient to nearby grocery stores, shopping, restaurants, and everyday services, with access to Winter Garden Village, area theme parks, and destinations throughout Central Florida.

7712 Fordson Lane, Windermere

Listing courtesy of KELLER WILLIAMS CLASSIC. murraycoleman@kw.com

$659,000
4 Beds 4 Baths O6426217 MLS
Price Improvement! Amazing opportunity to own this beautiful two-story single-family home located in the highly sought-after Lake Sawyer Enclave at Berkshire Park. Built in 2010 and meticulously maintained, this spacious home features 4 bedrooms, 3.5 bathrooms, and an ideal layout for both everyday living and entertaining. The home's attractive stone elevation and covered front porch create wonderful curb appeal and offer the perfect spot to enjoy your morning coffee. Step inside to a welcoming formal living room filled with natural light that flows seamlessly into the formal dining room, providing an elegant space for gatherings. Whether you're entertaining guests in the formal areas or relaxing in the spacious family room, this home offers plenty of room for everyone. The open-concept kitchen is a chef's dream, featuring granite countertops, 42-inch cabinets with crown molding, dark stainless steel appliances, and an oversized center island with ample prep space and bar seating. The adjoining breakfast nook provides a cozy space for casual meals. Conveniently located just off the kitchen are the garage entrance and a guest half bath tucked neatly beneath the staircase. Step outside to the covered, screened lanai and enjoy Florida's beautiful weather year-round. Large sliding glass doors fully open to seamlessly blend the indoor and outdoor living spaces, making it ideal for entertaining. The fully fenced backyard provides a safe place for pets to play, while the paver patio offers the perfect setting for relaxing around a fire pit on cool winter evenings. All four bedrooms are located upstairs for added privacy. The spacious primary suite features a tray ceiling, a large walk-in closet, and an ensuite bathroom with dual vanities, a garden tub, and a separate walk-in shower. Two secondary bedrooms share a convenient Jack-and-Jill bathroom, while the fourth bedroom includes its own private ensuite bathroom, making it ideal for guests or multigenerational living. Residents of Lake Sawyer Enclave enjoy outstanding community amenities, including a community pool, tennis courts, and a playground. Conveniently located just minutes from Walt Disney World and other major attractions, this home also offers easy access to the shopping, dining, and entertainment of Winter Garden Village, as well as major highways including SR 429, SR 408, and Florida's Turnpike. Please note: The interior photos showing furniture and décor have been virtually staged to illustrate the home's potential. Schedule your private showing today!

7537 Brofield Avenue, Windermere

Listing courtesy of SUNSHINE GROUP USA, INC. 321-394-5749

$1,090,000
4 Beds 4 Baths O6425171 MLS
Virtually Staged. One or more photo(s) was virtually staged. *** BRAND NEW ROOF AUG 2026 *** This is your opportunity to own a home in Keene's Pointe, a 24-hour guard-gated golf community on the Butler Chain of Lakes and home to the Golden Bear Club. Built by David Weekley and proudly offered by its original owner, this 4-bedroom, 4-bathroom home offers 3,646 square feet of flexible living space, including a dedicated home office, a flex room, and a spacious upstairs bonus room that could serve as a potential fifth bedroom, media room, or game room. Upstairs is also equipped with a full bathroom. A tandem three-car garage provides room for multiple vehicles, a golf cart, additional storage, or a workshop area. Inside, the thoughtfully designed floor plan begins with a formal dining room and dedicated home office just off the foyer. A secondary bedroom and full bathroom are conveniently located near the front of the home, while the open-concept family room and kitchen create the heart of the home. The kitchen features a center island, cabinetry, and countertop space. There is an existing electric range, but the community is connected to natural gas, offering the option to convert the existing electric range. Sliding glass doors open to the covered lanai and private backyard, extending the living space outdoors. The spacious first-floor primary suite offers plenty of room for a sitting area or reading nook. The primary bathroom features dual vanities, a walk-in shower, garden tub, and a spacious closet. Two additional bedrooms are privately situated on the opposite side of the home and are separated by a flex room, making it ideal as a study area, hobby space, or additional sitting room. A full bathroom with direct access to the covered lanai completes this wing of the home. Residents of Keene's Pointe enjoy private boardwalks to Lake Tibet of the Butler Chain of Lakes, community boat ramp to Lake Burden, four playgrounds, scenic green spaces, and neighborhood events. Optional membership to the Golden Bear Club offers championship golf course, tennis, a swimming pool, fitness center, dining, and an active social calendar. In order to utilize these amenities, a Golden Bear Club membership is needed. Conveniently located near Walt Disney World, shopping, dining, everyday conveniences and services, this home offers an opportunity to enjoy the lifestyle and amenities of Keene's Pointe. Disclosure: Artificial Intelligence has been utilized in public remarks and removal of some personal property.

8344 Bowden Way, Windermere

Listing courtesy of ALIGN REAL ESTATE LLC. 305-389-2922

$375,000
3 Beds 3 Baths TB8517100 MLS N/A BLDG.
Virtually Staged. This one has it all! Welcome home to this beautifully updated townhome in the highly sought-after Summerport community, where charm, comfort, and picturesque water views come together to create an exceptional living experience. From the moment you arrive, you'll be captivated by the home's inviting curb appeal, featuring a spacious front porch, attractive architectural details, elegant exterior lighting, and landscaping that enhances its timeless character. Inside, you'll discover a bright and welcoming interior highlighted by fresh paint, stylish luxury vinyl plank flooring throughout, and thoughtfully designed living spaces that offer both comfort and functionality. The well-appointed kitchen features crisp white cabinetry, stainless steel appliances, and ample storage, creating the perfect setting for everything from casual meals to entertaining guests. The open-concept layout flows seamlessly into the living and dining areas, while ceiling fans throughout the home provide added comfort and energy efficiency. Large windows invite natural light inside and frame beautiful views of the lake, creating a peaceful backdrop for everyday living. Additional highlights include generous garage parking and a desirable location within one of the area's most established communities. Enjoy easy access to community amenities including parks, clubhouse, community pool, tennis and basketball courts, all while coming home to tranquil water views and a welcoming neighborhood atmosphere. This exceptional Summerport home offers the perfect blend of style, convenience, and scenic beauty—don't miss your opportunity to make it yours.

5579 Somersby Road, Windermere

Listing courtesy of HOMESMART. 407-476-0461

$330,000
2 Beds 3 Baths O6424774 MLS 10430 BLDG.
Welcome to this beautifully maintained 2-bedroom, 2.5-bath townhome-style condominium nestled in the gated community of Oasis Cove at Lakeside Village in the heart of Windermere. Offering the perfect blend of comfort, style, and convenience, this move-in ready home features an open-concept floor plan with abundant natural light, creating an inviting space for both everyday living and entertaining. Residents of Oasis Cove enjoy resort-style amenities, including a community pool, fitness center, playground, clubhouse, and beautifully maintained grounds, all within a secure gated entrance. In addition to the resort-style amenities the association fees also include water, internet, cable, ground maintenance and exterior maintenance for all homes. Ideally located just minutes from Disney, Horizon West, Winter Garden Village, major highways, shopping, dining, and top-rated schools, this home offers easy access to everything Central Florida has to offer. Whether you're looking for your primary residence, a second home, or an investment opportunity, this exceptional property checks all the boxes. Don't miss your chance to own a beautiful home in one of Windermere's most desirable communities—schedule your private showing today! *New Roof + New HVAC!!*

14030 Sparkling Cove Lane Unit 603, Windermere

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211

$2,500,000
6 Beds 4 Baths O6418226 MLS
MULTI-GENERATIONAL LUXURY LAKEFRONT LIVING. Welcome to 1629 Hempel Avenue, a private lakefront retreat set on more than one gated acre along Lake Olivia, an approximately 88-acre, spring-fed lake with private access. Located in the desirable Gotha/Windermere area, this exceptional property offers rare peace and privacy while remaining convenient to Southwest Orlando’s renowned theme parks, premier shopping, Downtown Orlando, Orlando International Airport, highly regarded schools, and the Florida Turnpike. Mature trees, lush gardens, and thoughtfully designed outdoor spaces create a setting that feels secluded, established, and distinctly Florida. An antique church door provides a memorable entrance, setting the tone for a residence that blends refined finishes, distinctive character, and comfortable everyday living. The main residence features four bedrooms, two full bathrooms, and an expansive open-concept living area designed for entertaining while showcasing beautiful lake views. The oversized great room offers multiple gathering spaces, including a billiards area, a large television and game-day space, a generous dining area, and an impressive chef-inspired kitchen. At the center of the kitchen is an abundant quartz-topped island offering extensive workspace, seating, and a natural gathering place where guests can connect while meals are prepared. High-end flooring throughout the main home includes polished ceramic tile, travertine, and solid wood, while newer energy-efficient windows and doors enhance comfort and efficiency. The primary suite is a magazine-worthy addition created as a private lakeside sanctuary. Cathedral ceilings, polished ceramic tile flooring, expansive lake views, and a flexible sitting or exercise area create an open and relaxing environment. Two oversized custom closets provide exceptional storage. The luxurious bathroom features floor-to-ceiling ceramic tile, quartz countertops, an oversized porcelain soaking tub, and a spacious walk-in shower room. Four distinctive outdoor living areas invite you to enjoy the property throughout the year. Gather around the fire in the stone-paver garden area, relax within the private walled courtyard surrounded by potted plants and the soothing sound of a water fountain, or spend the day along the expansive backyard and private boat dock. The recently updated infinity-edge pool and heated spa overlook the lake, creating a resort-style setting for relaxing, entertaining, and enjoying unforgettable sunsets. A separate guest residence adds tremendous flexibility and privacy. Complete with two bedrooms, two bathrooms, a kitchen, and a living area, it is ideal for multigenerational living, extended guests, or an on-site caretaker. A private gated driveway and abundant parking accommodate multiple vehicles with ease. Combining two complete residences, more than an acre of lakefront land, exceptional outdoor living, mature landscaping, and private access to Lake Olivia, this one-of-a-kind estate offers a lifestyle rarely available in Central Florida.

1629 Hempel Avenue, Windermere

Listing courtesy of COLDWELL BANKER REALTY. 407-352-1040

$629,900
4 Beds 3 Baths O6423949 MLS
Situated on a distinguished homesite in one of Windermere's most sought after locations, 13328 Overstreet Road impresses right when you pull into the oversized 6+ CAR PAVER DRIVWAY with parking for up to six vehicles. If any of those vehicles are electric, you can charge them using the installed TESLA CAR CHARGER and save $$ on the electric bill with the PAID-OFF SOLAR PANELS. This home defines exceptional value and modern efficiency. At the heart of the home, the GOURMET KITCHEN is an entertainer's dream, with not one, but two center islands, ample solid WOOD CABINETS with crown molding, granite counters, and a tile backsplash. A stainless steel appliance package complements these features. A spacious dining area, family room, a mini mudroom off the garage, and a multipurpose space with additional cabinetry perfect for a small office, coffee bar, or wine bar. If you are looking for some multigenerational space, take advantage of the downstairs ensuite, which includes built-in closet organizers, a new vanity and toilet and a walk in shower. There is no carpet; the entire first floor has ceramic tile and the stairs and upstairs feature newly installed hardwood flooring. Luxurious master suite provides ELECTRIC BLINDS to let the light in and out at your fingertips, a perfectly organized walk in closet with custom built ins plus a double sink vanity with vessel sinks, modern light framed mirrors and a remodeled huge walk in shower complete with a shower wand, RAINHEAD SHOWER  and pebble stone floor. The second floor also offers a tremendous bonus/game room, media lounge, office or fitness studio along with 2 additional bedrooms, a full bath, and a laundry room with its own built-in sink and cabinet. Additional interior upgrades include plantation shutters on the first floor, an electric blind to the exterior and a digital thermostat. Exterior features include a SCREEN ENCLOSED LANAI  overlooking the fully fenced backyard for quiet comfort, privacy and shade from the yard's mature landscaping. Pavers line the back patio, making it possible to step right outside to both grill and dine al fresco during the temperate fall, winter, and spring months here in Central Florida. Additional features include YEAR ROUND HOLIDAY LIGHTING installed on the home making you ready for every season with the flip of a switch. Neighborhood features include a community pool complete with lounge chairs and a covered pavilion, a basketball court, a tennis court, a putting green, playgrounds covered from the sun or rain, and plenty of green space. LOCATION BENEFITS include easy access to DISNEY, SR 429, SR 408 to Downtown Orlando, Florida Turnpike, I4, shopping, restaurants and much more! Combining sophisticated finishes, versatile living spaces, and cutting-edge energy-conscious upgrades, this exceptional Windermere residence offers a lifestyle as impressive as the home itself.

13328 Overstreet Road, Windermere

Listing courtesy of RE/MAX PRIME PROPERTIES. 407-347-4512

$539,900
3 Beds 2 Baths O6423262 MLS
WELCOME HOME! NEW IMPROVEMENTS! Nestled beneath majestic oak trees in one of Windermere's most desirable communities, this well-maintained 3-bedroom, 2-bath home sits on a quarter of an acre and offers the perfect blend of comfort, privacy, and location. Situated in the highly sought-after 34786 zip code, this exceptional residence features a popular split-bedroom floor plan with 1,819 square feet of thoughtfully designed living space. Silver Woods is located in the center of SW Orlando, close to Downtown Windermere, Restaurant Row, Winter Garden Village, Downtown Winter Garden, churches, schools, shopping, and more. As you enter the front door, you will be impressed with the open floor plan. New paint, new carpet, and neutral tile create a light and bright environment. Step inside to discover spacious living and dining areas that flow seamlessly into the heart of the home. The living room looks out onto the huge patio and backyard. The kitchen offers abundant cabinetry, granite countertops, ample workspace, and overlooks the main living areas, making it ideal for everyday living. Enjoy the family room, which opens to a covered, screened lanai via sliding doors, creating an incredible outdoor living space perfect for relaxing, entertaining, or simply enjoying the tranquil backyard surrounded by mature trees. The oversized, park-like shared fenced backyard provides exceptional privacy and plenty of room for gardening, play, or creating your own outdoor oasis. Let your imagination create the perfect Pool/Spa area with a summer kitchen, fire-pit, and more. The primary bedroom features sliding doors to the expansive lanai, and the en-suite features a Tub, a newer double-sink vanity, and a NEW WALK-IN TILED SHOWER! A split-bedroom plan is perfect for today's busy family, featuring two bedrooms and a hall bath with a shower/tub. Recent improvements, including a NEW ROOF, HVAC (2016), New Garage Door (2016), Septic (2021), Electric Panel (2017), Interior paint (2026), Front Sod (2026), and Carpet (2026) in the main living areas, make this home move-in ready while still offering opportunities for a new owner to personalize and add value over time. The community offers a park and a tennis court for the residents. Ideally located just minutes from top-rated Windermere schools, shopping, dining, churches, world-famous theme parks, major highways, and Orlando's many entertainment destinations, this home offers the perfect balance of peaceful neighborhood living and everyday convenience. Don't miss your chance to make this Windermere gem your next home- schedule your private showing today!

9433 Palm Tree Drive, Windermere

Listing courtesy of COLDWELL BANKER REALTY. 407-352-1040

$6,700,000
8 Beds 10 Baths O6422852 MLS
Virtually Staged. Welcome to an extraordinary new construction waterfront estate built by Element Home Builders, located in the prestigious 24-hour guard gated community of Keene’s Pointe. Situated on a private cul-de-sac, this one of a kind residence rests on a spectacular 0.78 acre homesite with 518 feet of combined waterfront overlooking a serene pond and the beautiful waters of Lake Burden. Offering 8,133 square feet under air and 10,971 total square feet, this exceptional home features 8 bedrooms, 7 full bathrooms, and 3 half bathrooms with unparalleled craftsmanship and luxury finishes throughout. A grand marble foyer welcomes you with soaring ceilings, designer lighting, wood beams, and rich solid oak flooring. The stunning chef’s kitchen features custom solid wood cabinetry, stunning countertops, Thermador paneled refrigerator and freezer with white wine refrigeration, Wolf range, built-in convection oven, microwave, and a custom exhaust hood. The expansive great room showcases a natural stone fireplace and wall to wall sliders that open to breathtaking views of the infinity edge saltwater pool, spa, backyard oasis, and Lake Burden. The luxurious primary suite offers panoramic water views, custom illuminated walk-in closets, a spa inspired bathroom with a massive shower, designer fixtures, and a freestanding soaking tub. Additional highlights include a temperature controlled wine cellar, hidden elevator, executive study with custom built-ins, five spacious main level bedrooms, and a spectacular second floor featuring a private gym with reinforced insulation, custom theater, loft with kitchenette, balcony overlooking the water, and three ensuite bedrooms. Outdoor living is designed for entertaining with your summer kitchen including a heavy duty grill and hood, motorized screens for the entire lanai, multiple gathering areas, fire pit, private putting green, and a nature path leading to your covered boat dock with boat lift for endless Lake Burden adventures on a 125 acre skiable lake. A four-car garage with built in ceiling lighting tracks and electric vehicle charging completes this exceptional residence. Keene’s Pointe offers an unmatched lifestyle with the Golden Bear Club, featuring a championship golf course, clubhouse, fitness center, tennis courts, resort-style pool, and numerous parks and recreation areas. Ideally located just minutes from Walt Disney World, world class dining, shopping, and top rated schools, with close proximity to Windermere Preparatory School. This rare never been lived in lakefront estate is being offered for the first time and represents a unique opportunity to own one of Central Florida’s finest custom homes. Be sure to click on the virtual tour links.

8342 Boyla Court, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396

$1,150,000
4 Beds 3 Baths O6422132 MLS
Nestled within the highly sought-after Windermere Downs community this Lake-Access Residence, sitting on .74 acres, offers the ultimate Florida lifestyle surrounded by canopy-shaded, oak tree-lined streets. A walkway lined with custom pavers leads to the front door, where you're welcomed by the formal living and dining rooms on the right. Large bay windows let in plenty of natural light, creating a bright and inviting space. A barn door opens to the kitchen, which features travertine flooring, a gas stove, and stainless steel appliances—great for home cooking or entertaining. The living room is a cozy gathering space, with three skylights bringing in extra light and an Authentic Old Chicago Brick fireplace that adds warmth and character. The primary bedroom is spacious, with French doors that open to the screened-in pool lanai, offering easy access to outdoor living. The primary bathroom includes a Kohler clawfoot tub and Kohler fixtures, adding a touch of quality and comfort. Out back, the screened-in pool with travertine deck and patio provides a great spot to relax, while the larger open travertine patio off of the kitchen is perfect for hosting family and friends. The backyard is full of greenery, offering both beauty and privacy and an irrigation well. Home includes a 1,000 Underground Large Gas Tank and Full House Propane Generator and a hybrid water heater. A two-car attached garage is complemented by a large detached deep second two-car garage, perfect for extra parking, storage, or keeping your favorite lake-living toys. Living in Windermere Downs means access to a private community boat ramp, where you can launch your boat and explore Lake Down and the Butler Chain of Lakes. The community amenities include a dock with a roped-off swim area, tennis courts, pickleball courts, community park, playground—plenty of options for outdoor fun. Recent updates include whole house re-pipe (2026), freshly painted exterior and new soffit (2026).

2009 Woody Drive, Windermere

Listing courtesy of REVEL REALTY LLC. 407-876-6448

$560,000
3 Beds 2 Baths O6420991 MLS
Welcome to this charming and inviting home nestled in the highly desirable Lake Sawyer South community in Windermere. As you drive through the neighborhood, you'll immediately appreciate the mature landscaping, beautiful tree-lined streets, and peaceful atmosphere that make this communityso special. Upon arrival, you're greeted by a spacious covered front porch — the perfect place to relax and enjoy the Florida lifestyle. Step inside to a welcoming, wide foyer that opens to a bright and airy living room featuring soaring ceilings and an abundance of natural light. Two secondary bedrooms are thoughtfully positioned at the front of the home, offering privacy and flexibility for family members, guests, or a home office. The formal dining room is enhanced by a large window that fills the space with beautiful natural light, creating an inviting setting for entertaining. The open-concept kitchen overlooks the living room, making it ideal for gathering with family and friends. It also includes a cozy breakfast nook, perfect for casual everyday meals. Privately located at the rear of the home, the spacious primary suite is filled with natural light from three large windows. The en-suite bathroom features dual vanities, a soaking tub, a separate walk-in shower, a walk-in closet, and an additional linen closet for extra storage. Sliding glass doors from the living room lead to a covered and screened lanai and a fenced backyard with a paved patio, providing the perfect space for outdoor dining, entertaining, or simply unwinding. Offering 1,706 square feet of living space, this well-maintained home features 3 bedrooms, 2 bathrooms, a formal dining room, an open living room, a functional kitchen, a dedicated laundry room, and a two-car garage. Conveniently located just minutes from Publix, coffee shops, dinners, restaurants, shopping, personal storage facilities, and schools. This home combines comfort, convenience, and an exceptional Windermere location. Don't miss the opportunity to make this beautiful and welcoming home your own—schedule your private showing today! The existing solar panel financing is transferable to qualified buyers, offering the opportunity to enjoy energy savings without the upfront installation cost.

13219 Charfield Street, Windermere

Listing courtesy of DENIZ REALTY PARTNERS LLC. 407-704-0780

$325,000
3 Beds 2 Baths O6421614 MLS 8168 BLDG.
Virtually Staged. Imagine coming home to a resort-style community just minutes from Walt Disney World! This beautiful 3 Bed + 2 Bath top-floor unit is located in the highly sought-after Horizon West area of Windermere, where comfort, convenience, and an exceptional location come together. Perfectly situated directly across from the clubhouse with easy elevator access, this bright and spacious home offers relaxing views from the private screened balcony overlooking the community's extensive amenities. The open, split floor plan features tile flooring throughout the main living areas, carpet in the bedrooms, and gorgeous crown molding. The lovely kitchen has granite countertops, 42" maple cabinetry, quality appliances, upgraded fixtures, and a large walk-in pantry. Lakeside's amenities include two resort-style pools, fitness center, volleyball courts, and a spacious clubhouse. Located just minutes from Disney, Lake Side Shoppes, Hamlin Town Center, tons of restaurants and top-rated schools! Call today to schedule a viewing!

8168 Boat Hook Loop Unit 724, Windermere

Listing courtesy of ROMAN REALTY GROUP, LLC. 407-876-1990

$2,099,900
4 Beds 6 Baths O6421211 MLS
Stunning Lakefront Mediterranean Retreat on Lake Whitney! Discover this spacious, breathtaking lakefront home nestled along the banks of Lake Whitney. Enjoy spectacular views from your private dock, deck, boat lift, & open-air boathouse, perfect for water sports, lake-side entertaining, BBQs, & catching mesmerizing sunsets. Ski friendly Lake Whitney is a great spot for wakeboarding, jet skiing or water skiing. Designed for the ultimate lake lifestyle, this home features Tuscan-inspired landscaping, an infinity pool & spa, plus expansive outdoor entertaining areas. Host unforgettable gatherings with an outdoor grill & kitchen, patio dining, outdoor fireplace, & comfortable seating, all under a screened enclosure for year-round enjoyment. The gourmet kitchen is a chef’s dream, equipped with ultra-premium Viking appliances; including a double oven, dishwasher, gas cooktop, refrigerator, & wine cooler. Granite countertops, a spacious island, walk-in pantry, dual sinks, & open layout seamlessly connect to the living & dining areas. A full-size laundry room with front-loading washer and dryer, sink, & tall cabinets adds convenience. The ground level offers a formal dining room & an office/library with built-in shelving. The massive primary suite boasts stunning lakefront views, while the luxurious master bathroom features a walk-in closet, granite countertops, dual garden baths with massage jets, a sauna, and privacy toilet and bidet. Elegant French doors lead into a welcoming foyer, with soaring ceilings and a grand staircase leading upstairs. The 2nd floor includes 3 bedrooms, 3.5 bathrooms, & a versatile game room or theater with built-in entertainment & a microwave. Three bedrooms have private baths, & an elevated outdoor covered patio offers additional lake views with ceramic tile flooring. An oversized three-car garage with electric doors, double water heaters, & ample storage completes this exceptional home. Experience the charm of Tuscany combined with the luxury of lakefront living in Central Florida! Schedule your private tour today and make this dream home yours! Sold as-is, where-is. No Seller’s disclosures. Seller is making no warranties or representations of property condition. Room dimensions are approximate & should be independently verified. Proof of funds/pre-approval letter required with all offers. Buying party is responsible for verifying whether property condition will qualify for buyer’s specific loan program. If applicable, HOA or Condominium monthly dues may be subject to changes, special assessments & must be verified by buyer. Monthly dues often adjust on January 1st of each year. Some condominiums may also charge an initial “Capital Contribution” payable at closing. MLS information deemed reliable, but not guaranteed. Parties are advised to verify. The seller requires a 10 DOM holding period prior to entertaining any offers. *Per our seller, please ensure all potential buyers view the interior of the property prior to submitting offers. Agents must always accompany buyers during showings. Seller will not entertain sight-unseen offers. Please factor any repair estimates into the offer.* There's a 7-minute interior video walk-through available under Virtual Tour in MLS.

1238 Lake Whitney Drive, Windermere

Listing courtesy of JASON CRANE REAL ESTATE LLC. 321-206-6937

The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of MLS Now and updated as of . Real estate listings held by brokerage firms other than Coldwell Banker Realty are marked with the Internet Data Exchange logo and detailed information about them includes the name of the listing broker(s).
IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
All information provided is deemed reliable but is not guaranteed and should be independently verified. © 2026 MLS Now. All Rights Reserved.